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2 article(s) from Sugiishi, Tsuyuka

Nucleophilic fluoroalkylation/cyclization route to fluorinated phthalides

Masanori Inaba,
Tatsuya Sakai,
Shun Shinada,
Tsuyuka Sugiishi,
Yuta Nishina,
Norio Shibata and
Hideki Amii

Beilstein J. Org. Chem. 2018, 14, 182–186, doi:10.3762/bjoc.14.12

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Scheme 1: Phthalide and fluorinated phthalides (1).

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Scheme 2: Plausible reaction mechanism for the formation of phthalide 1a.

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Scheme 3: Synthesis of fluorinated phthalides 1.

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Scheme 4: Asymmetric synthesis of 1a using a chiral auxiliary.

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Scheme 5: Catalytic asymmetric synthesis of 1a.

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Full Research Paper

Published 19 Jan 2018

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Carbon–carbon bond cleavage for Cu-mediated aromatic trifluoromethylations and pentafluoroethylations

Tsuyuka Sugiishi,
Hideki Amii,
Kohsuke Aikawa and
Koichi Mikami

Beilstein J. Org. Chem. 2015, 11, 2661–2670, doi:10.3762/bjoc.11.286

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Scheme 1: Trifluoromethylation using trifluoroacetate.

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Scheme 2: Decarboxylative pentafluoroethylation and its application.

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Scheme 3: Trifluoromethyation with trifluoroacetate in a flow system.

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Scheme 4: Trifluoromethylation of 4-bromotoluene by [(NHC)Cu(TFA)].

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Scheme 5: Trifluoromethylation of aryl iodides with small amounts of Cu and Ag₂O. ^aThe yield was determined b...

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Scheme 6: C–H trifluoromethylation of arenes using trifluoroacetic acid.

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Scheme 7: CF₃Cu generated from chlorofluoroacetate and CuI.

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Scheme 8: [¹⁸F]Trifluoromethyation with difluorocarbenes for PET. ^aRadiochemical yield determined by HPLC.

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Scheme 9: Trifluoromethylation with trifluoroacetate and copper iodide.

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Scheme 10: Preparation of trifluoromethylcopper from trifluoromethyl ketone.

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Scheme 11: Trifluoromethylation of aryl iodides. ^aIsolated yield. ^b1 equivalent each of CF₃Cu reagent and 1,10...

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Scheme 12: Pentafluoroethylation of aryl bromides. ^aYield was determined by ¹⁹F NMR analysis using benzotriflu...

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Scheme 13: Perfluoroalkylation reactions of arylboronic acids. ^aIsolated yield. ^bDMF was used instead of tolue...

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Scheme 14: Trifluoromethylation with silylated hemiaminal of fluoral.

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Scheme 15: Catalytic trifluoromethylation with a fluoral derivative.

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Scheme 16: The scope of Cu-catalyzed aromatic trifluoromethylation. The yield was determined by ¹⁹F NMR analys...

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Scheme 17: Plausible mechanism of Cu-catalyzed aromatic trifluoromethylation [53].

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Review

Published 18 Dec 2015

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